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Chemical compound
Methitural
ATC code
5-[2-(methylsulfanyl)ethyl]-5-(2-pentanyl)-2-thioxodihydro-4,6(1H ,5H )-pyrimidinedione
CAS Number
PubChem
CID
ChemSpider
UNII
ChEMBL
Formula C 12 H 20 N 2 O 2 S 2
Molar mass 288.42 g·mol−1 3D model (
JSmol )
O=C1NC(=S)NC(=O)C1(C(C)CCC)CCSC
InChI=1S/C12H20N2O2S2/c1-4-5-8(2)12(6-7-18-3)9(15)13-11(17)14-10(12)16/h8H,4-7H2,1-3H3,(H2,13,14,15,16,17)
Key:KEMCRVSPPRNENL-UHFFFAOYSA-N
Methitural (
INN ; Neraval , Thiogenal ), or methitural sodium , also known as methioturiate , is a
barbiturate
derivative which was marketed in the 1950s in
Europe (in
Germany and
Italy ) as an ultra-short-acting
intravenous
anesthetic .
[1]
[2]
[3]
Synthesis
Methitural synthesis: Zima, Von Werder,
U.S. patent 2,802,827 (1957 to E. Merck).
A somewhat more complex side chain is incorporated by alkylation of the carbanion of the substituted
cyanoacetate (1 ) with 2-chloroethylmethyl sulfide (2 ). Condensation of the resulting cyanoester (3 ) with thiourea followed by hydrolysis of the resulting imine affords methitural.
See also
References
Alcohols
Barbiturates
Benzodiazepines
Carbamates
Flavonoids
Imidazoles
Kava constituents
Monoureides
Neuroactive steroids
Nonbenzodiazepines
Phenols
Piperidinediones
Pyrazolopyridines
Quinazolinones
Volatiles /
gases Others/unsorted
3-Hydroxybutanal
α-EMTBL
AA-29504
Alogabat
Avermectins (e.g.,
ivermectin )
Bromide compounds (e.g.,
lithium bromide ,
potassium bromide ,
sodium bromide )
Carbamazepine
Chloralose
Chlormezanone
Clomethiazole
Darigabat
DEABL
Deuterated etifoxine
Dihydroergolines (e.g.,
dihydroergocryptine ,
dihydroergosine ,
dihydroergotamine ,
ergoloid (dihydroergotoxine) )
DS2
Efavirenz
Etazepine
Etifoxine
Fenamates (e.g.,
flufenamic acid ,
mefenamic acid ,
niflumic acid ,
tolfenamic acid )
Fluoxetine
Flupirtine
Hopantenic acid
KRM-II-81
Lanthanum
Lavender oil
Lignans (e.g.,
4-O-methylhonokiol ,
honokiol ,
magnolol ,
obovatol )
Loreclezole
Menthyl isovalerate (validolum)
Monastrol
Niacin
Niacinamide
Org 25,435
Phenytoin
Propanidid
Retigabine (ezogabine)
Safranal
Seproxetine
Stiripentol
Sulfonylalkanes (e.g.,
sulfonmethane (sulfonal) ,
tetronal ,
trional )
Terpenoids (e.g.,
borneol )
Topiramate
Valerian constituents (e.g.,
isovaleric acid ,
isovaleramide ,
valerenic acid ,
valerenol )